The folks crossing the country or the world non stop are usually between a degree and their first job, are retired, or have a substantial trust fund or other income. A few are making it on assets they've acquired after working a while. A few others seem to do ok by siphoning off travel funds from donations to some charitable cause. A few are their own bosses. A few wrangle long sabbaticals. A few more are competent bums with no job to worry about.
The working stiff who gets the American standard 2 weeks, well he can pedal for about 14 days, and take some interim mini-tours to scratch the itch. Till one or more of the above takes affect.
As a famous person once said "I feel your pain."